Castanospermine analogues

Winchester BG Cenci di Bello I, Richardson AC, Nash, RJ, Fellows LE, Ramsden NG Fleet G. (1990) The structural basis of the inhibition of human glycosidases by castanospermine analogues. Biochem J 269 227-231. 

Castanospermine analogues 127 and 128 have been synthesized in many steps from a chirally unresolved pyrrolidinone. ... 

Several sugar-derived N-hetcrocycles have been reported castanospermine analogues 29-31, 1-deoxynojirimycin.HQ, the carbohydrate-derived dihydroisoquinoline-/V-oxide 32, and lV-trideca-5,7-diyne-D-glucosainine (a super-structure fomiing synthetic glycolipid) at 295, 100 and 20K.100... 

Guanidinium and isothiourea derivatives such as 46 and 47 were also reported that exhibited potent and selective (3-glycosidase inhibitory activity, in contradiction with the previous castanospermine analogues depicted above. Noteworthy, sulfamide-type indolizidines such as 48, in which the thiourea moiety has been replaced by a sulfamide group, were also described and found to be modest a-mannosidase inhibitors... 

Burgess, K. Henderson, I. 1990. A new approach to swainsonine and castanospermine analogues. Tetrahedron Lett. 31 6949-6952. 

Martin and co-workers have utilized 1-lithiofuran addition as a key carbon-carbon bond-forming step for construction of 8,8a-di-ep/-castanospermine. Intermediate furan aduct 233 is elaborated to 234 via furan oxidation and thence to the castanospermine analogue 235 (Scheme 41). 

A number of C8 modified castanospermine analogues 237 have been prepared by displacement of 8-sulfonate derivative 236. Retention of stereochemistry is... 

The synthesis of unusual variants of castanospermine and congeners has been an area of activity this year. The silylated diene 160 (from D-arabinose) undergoes a hetero Diels-Alder reaction to provide the pyrrolo-castanospermine analogue 161 (Scheme 33), and the branched... 

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